So, after a few more days crawling around the core, I think checking for a live REPL connection isn't currently possible. One exception to that is WebREPL; that would be doable by checking for the file stats. Of course I caveat all of this with "I am very possibly wrong", but here is how I've come to that conclusion.

Starting at circuitpython/main.c:L#119, the boot code checks serial_connected(), and if it is, it prints out the startup info to the REPL. (there is at least one other place where the serial is checked before sending/listening to REPL...but it's all rapidly congealing inside my brain and I forgot where I saw it)
serial_connected() is in circuitptyhon/ports/????/supervisor/serial.c for each port.
- atmel-samd: serial_connected returns the result of usb_connected() (see above comment)
- nrf: serial_connected() returns True...always. As in, it's hardcoded: return true; (L#66)
- esp8266: actually uses it's own main.c which has a slightly different method, but it works the same by just checking for a serial connection. There is also the added use of WebREPL.

In summary, there is no active REPL state information; it all just assumes if the serial connection, through USB/BLE/Web, is active then we should send and listen for REPL activity.

I'll keep digging into it, but I think I've hit bedrock...

I've got USB check running on SAMD. I'll start working the others soon.

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